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Methylboronic Acid → Ethyl 3-(5-(2-formyl-3-methyl-5-(trifluoromethyl)phenyl)picolinamido)propanoate

HRID 405252
Notes
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Reaction equation

HRID 405252 reaction equation
Cl[C:2]1[C:3]([CH:28]=[O:29])=[C:4]([C:12]2[CH:13]=[CH:14][C:15]([C:18]([NH:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:19])=[N:16][CH:17]=2)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[CH3:30]B(O)O>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:28]([C:3]1[C:2]([CH3:30])=[CH:7][C:6]([C:8]([F:11])([F:10])[F:9])=[CH:5][C:4]=1[C:12]1[CH:13]=[CH:14][C:15]([C:18]([NH:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:19])=[N:16][CH:17]=1)=[O:29]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 139377Methylboronic AcidHCID 86674266Ethyl 3-(5-(3-chloro-2-formyl-5-(trifluoromethyl)phenyl)picolinamido)propanoate

Product 1

HCID 86674283Ethyl 3-(5-(2-formyl-3-methyl-5-(trifluoromethyl)phenyl)picolinamido)propanoate

Reagents, catalysts & solvents 3

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst
HCID 962
Water
Solvent
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

Ethyl 3-(5-(3-chloro-2-formyl-5-(trifluoromethyl)phenyl)picolinamido)propanoate (150 mg, 0.35 mmol), methylboronic acid (31 mg, 0.53 mmol), Pd(dppf)Cl2 (34 mg, 0.05 mmol) and K3Pa4hydrate (322 mg, 1.40 mmol) were dissolved in 1,4-dioxane (2 mL) and the resulting mixture was heated to 90° C. After 10 h the resulting mixture was diluted with water and extracted with EtOAc. The combined organic extracts were dried (Na2SO4), concentrated, and purified via column chromatography to yield the title compound.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified via column chromatography

Sources & evidence

ORD record
ord-5d4007b31560479a90579701385cf45b
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08748624B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes